Harper is an AI-native commercial insurance company in San Francisco. We're not bolting AI onto insurance — we're rebuilding the entire business as software, on a simple bet: turning expert human judgment into compute is one of the largest transitions left to make, and a trillion-dollar industry still run 90% by hand is the place to prove it. We've grown ~100x in the last year and we move at that speed — on-site, in person, long days, very high standards. Almost no one joins Harper for insurance; they join to build the company that replaces how it works.
The role
This role works directly with the CEO on the hardest problems in the business, with a seat in everything substantive: biz ops, growth, strategic projects, investor materials, M&A diligence, and whatever becomes most urgent that week.
There is no fixed scope. That's not a warning — it's the design. The company is changing fast, and the job is to flex across it and take on whatever matters most right now. Week to week, the work shifts. We just closed our Series A, and the systems built now decide whether we go from tens of millions in premium to hundreds of millions, then billions. What you do here meaningfully moves that line.
The goal is for you to see every part of the business deeply. If you perform the way we think you can, the role evolves into whatever makes sense next — running a function, becoming a true right-hand, or using what you learned to go build your own thing.
What you'll do
Take the CEO's hardest problems. Direct access to everything that matters; scope shifts week to week based on what's most critical.
Build 0→1 systems. Across underwriting operations, customer experience, and risk evaluation — using AI to replace historically manual brokerage work.
Run deep analysis. Customer interactions, underwriting requirements, operational workflows; find patterns, lift conversion, increase throughput.
Bridge engineering, operations, and growth. Turn customer needs and market reality into product requirements and iteration.
Own problems end-to-end. Gather data, map the system, find the constraint, propose the fix, run the experiment, drive to done.
Run cross-functional initiatives. Coordinate across engineering, carriers, underwriters, and customers with speed and high quality.
Build the intelligence layer. Dashboards, metrics, and reporting that surface truth about throughput and efficiency.
Who you are
Raw analytical horsepower; you think in systems.
A bias toward action — you move toward execution, not away from it.
Energized by complexity rather than rattled by it.
You've worked in high-intensity analytical/operational roles (banking, consulting, PE, high-growth startups) and thrived.
You want exposure to every part of building a company — and you're willing to work for it.
Requirements: 2–5 years in high-intensity analytical or operational roles (IB, PE, management consulting, or equivalent startup experience); exceptional analytical skills (complex data, financial modeling, ambiguous problems); strong written and verbal communication; able to operate autonomously and context-switch fast; a track record of delivering under pressure; based in SF or willing to relocate immediately.
Nice to have: insurance, fintech, or regulated-industry experience; prior work directly with founders or C-suite; familiarity with AI/automation tooling; prior startup or 0→1 experience.
The honest day-to-day
We'll be direct, because this role attracts people who romanticize "working with the CEO" and underestimate the cost:
The scope never settles. What's urgent today may be irrelevant in two weeks. If you need a defined mandate and a stable roadmap, you will be miserable here. The constant context-switching is the work.
It's banking-analyst intensity, with higher stakes because it's real. Early starts, late finishes, on-site in SF, Mon–Fri (~5 AM–8 PM).
"Access to the CEO" means accountability, not status. You own outcomes on the hardest problems, often with incomplete information.
The ceiling is genuinely limitless for the right person — running a function, becoming a right-hand, or leaving to start your own company — but you earn it by absorbing chaos others can't, not by being adjacent to it.
Compensation & logistics
Salary: $150,000–$175,000 + performance bonuses & equity
Location: San Francisco, in-office. Based in SF or willing to relocate immediately.
Schedule: Monday–Friday, very early morning start, in-office 5 days a week.
Benefits: Uber commuter benefits; breakfast, lunch, and dinner provided; snacks, drinks, and coffee daily; free gym membership; health, dental, and vision insurance.
Process
Founder screen — initial fit and alignment
On-site day — meet the team, work through real scenarios
To apply
Send your resume and tell us about a time you owned something ambiguous and drove it to completion. If you're okay with the scope changing constantly and this being the hardest you've worked, the ceiling is limitless.